1. Field of the Invention
The present invention generally relates to a process for making allyloxytrifluoropropenes and homopolymers and copolymers thereof starting from fluoro olefins. More particularly, the present invention relates to a process for making compounds, such as, CF3CH═CHOCH2CH═CH2, CF3CH═CFOCH2CH═CH2, CF3CH═C(OCH2CH═CH2)2 and methallyl derivatives thereof from CF3CH═CHF or CF3CH═CF2 and allyl or methallyl alcohol.
2. Description of the Prior Art
Compounds containing allyloxy group are typically used as monomers for preparing siloxane polymers or as a CF3 building block. See, for example, Polymer Chemistry, (1995) 33(14), 2415-23, J. Polymer Sci. A: Polym. Chem (1997) 35, 1593-1604 and Chem. Commun., (1996), 57-58.
Uses of polymers derived from allyl ethers for UV curing, to films on various surfaces, for adhesives, coating, cladding and the like are described in J. Polym. Sci., Part A, Polym. Chem., 2002, 40, 2583-2590.
Allyloxypropene of the formula CF3CH2CFHOCH2—CH═CH2 is used as a monomer for making siloxane polymers, as described in the German Patent DE 3,138,235 A1 and in J. Fluorine Chem., (2005), 126, 281-288.
Relatively little is known about allyloxypropene polymers in general. U.S. Pat. No. 6,930,159 B1 describes some fluorinated allyl ether polymers. However, the structure of monomers used in the preparation of the polymers described in this patent is quite different from the allyloxypropene monomers described in the present invention.
Relatively little is known about allyloxypropenes described by the present invention. The only known example in this group is 1-allyloxy-3,3,3-trifluoropropene of the formula CF3CH═CH(OCH2CH═CH2) which is made from CF3CBr═CH2 with a base and catalytic amount of water.
This reaction proceeds by an elimination-addition mechanism through the formation of trifluoromethylpropyne as an intermediate followed by the addition of allyl alcohol to the so formed trifluoromethylpropyne (See Chem. Commun., (1996), 57-58).
However, large-scale preparation of allyloxytrifluoropropenes using this approach requires the use of CF3CBr═CH2 as a starting material, which is expensive and cumbersome to manufacture.
Compounds such as CF3CH═C(OCH2CH═CH2)2 with two allyloxy groups and polymers derived therefrom are unknown in the art.
Consequently, there is a need in industry to develop commercially feasible processes for making such compounds and exploring their properties and uses in various applications.
To achieve this objective, the present invention provides a process, which is practical and, as such, it is potentially useful commercially.